[JimDabell]

I haven't experienced any of that, but then I wouldn't use it for Windows in the first place and it doesn't sound like the kind of thing the OP is doing either.

The Salt provisioner doesn't bootstrap Salt every time, so it may be a bug with the Chef provisioner rather than something that's true of all provisioning. Isn't Chef installed by default on most base boxes anyway though? It sounds like you've hit an edge case that you can work around by installing Chef in your base box.

Snapshots and backing up VMs sounds a lot more hassle than Vagrant.

Same goes with Cask – I've never had it lose track of applications. It's hard to see how this could happen, as this mechanic is pretty simple – if it's in the directory, it's present, otherwise it's absent.